Watching the Detectives

He paused for a moment, clearing his throat as a light flush coloured his cheeks.

'You were so nice to me, no-one I've ever known has been so caring and positive about the way I look. I couldn't have done this without you and then, when we kissed, I just lost it. It didn't somehow feel like a man then, I was scared but so excited too. I was kissing someone I had fancied from the moment I saw you in that hospital and where I swore I would find the bastards who put you there.'

I took his hand, 'Baby...'

'Please, Philippa, let me finish. So, when you kissed me I just felt like something gave way inside me, I couldn't stop myself and wouldn't have wanted to anyway. Yes, I was confused when you sucked my cock, but not so confused that I wanted you to ever stop. I had never felt so turned on and excited by anything before, you really took me to a whole new level of pleasure and when we lay on the bed I knew I had see if I could go one step further, I needed to see if this was just me reacting to what you were doing or whether I could do something I would never have dreamt of. Well, I did and the earth didn't open up and swallow me, and God didn't strike me down. I wanted to make you happy, Philippa, and I liked it. I liked all of it, and I want to do it again. I don't know whether I've answered your question, but if you want me to leave now, I will.'

I took a moment before replying, and I saw apprehension in his eyes as I took his hand once more.

'Oh Tim, why on earth would you think I want you to leave? That was the most beautiful thing I have ever heard, I don't want you to leave.'

I reached out and hugged him, tears pricking the corners of my eyes. I felt his arms tentatively go around my back and then he was hugging me back.

'Thank you, Philippa, I was praying you would say that.'

'Did you really fancy me at the hospital? I must have looked bloody awful when you came in and did you know I was...'

'TG? Yeah, I knew. The hospital reported it as a hate crime, remember?'

'I must have stood there for about five minutes watching you before you woke up and you looked so helpless and beautiful while you slept. I think I fell for you then.'

It was my turn to blush scarlet at his words. 'Oh Tim, that's either very sweet or very spooky.'

He laughed, 'I prefer sweet.'

'But you knew I was TG and yet you say you fell for me? I'm sorry for asking this, but are you gay?'

He paused and looked down, 'I didn't think I was, but now? I don't know. I've had girlfriends for sure and never fancied men. But when I saw you, I knew that I was attracted to you, it was as simple as that. Does that make me gay?'

'I don't know either. Labels are for clothes in my book, not people. I've never worried about it and don't intend to start now.'

I kissed him and said, 'What I do remember is being very jealous of your eyelashes, but I was probably concussed at the time. Are you sure you still want to go on with this plan? I mean if you have any doubts, please tell me now.'

'No, more than ever I think I want to catch these two thugs for what they did to you and to stop them doing it again.'

I breathed a sigh of relief. 'OK,' I said, 'but I think we need to get clear a few ground rules. Firstly, these next two days will be completely feminine, if this is going to work you will need to immerse yourself as a woman. It isn't really about the clothes or the makeup, it's about thinking and acting as a woman at all times. I know it's going to be awkward but the more you believe you are a woman, the closer you will get to looking and acting like one. You're going to be Tina, not Tim, for the next two days and nights. Secondly, you will do as I say at all times, nothing we do will go outside this apartment, so it will just be between the two of us, is that clear?'

He looked a bit apprehensive, but nodded, so I went on, 'Thirdly, If, by tomorrow afternoon, we both agree that it feels right, then we can go out to a friendly pub I know which has a TG evening as a dry run so you can get to meet some of the girls you want to talk to. Is that OK?'

He gulped once and said, 'OK, but you'll be with me, right?'

'Oh yes, I'm not going to let my new girlfriend go out by herself.'

The first task was to teach Tim some makeup basics, not that I expected him to do it straightaway but I showed him the basics of a daytime makeup and with a lot of help and guidance and a couple of false starts, we got there. I was giggling a lot, which made Tim giggle too, so I thought he was enjoying this. he couldn't take his eyes off his reflection in the mirror, and he was fascinated by how much it had changed his face.

'Can I put the wig on please,' he asked, 'I don't like looking like a bloke wearing makeup.'

I helped him fit the wig and I could see the change in him immediately. The wig seemed to make him relax and the stiffness left his face and became softer right in front of me eyes.

He turned to me, 'Do you think I look pretty?'

I smiled and came up behind him so we could see both our faces next to each other in the mirror. I gave him a kiss on the cheek and said, 'Yes, I do think you look pretty, you have the most beautiful eyes and lashes, and very kissable lips.'

I leant in to kiss his lips and he moved away saying, 'Don't you dare, it will take me ages to do them again.'

I pouted and pretended to be upset, but inside I was cheering, for he was really getting into this. For clothes I wanted to select something that was feminine but not too tarty. The mistake a lot of new crossdressers make is to look like they should be standing on the street corner. It may fulfil their inner fantasy, but it makes them stand out like a Goth at choir practice.

I asked Tim if there was something he liked and he shyly picked up a navy and yellow floral print dress.

'I quite like this,' he said.

'Mmm, I approve, you have a good eye, Tina.' It had a round neck, short sleeves and a belt and I thought would suit Tina's straight up and down shape. It would also make the most of his legs, which I was beginning to think were his best feature, OK, second best feature, if you get my meaning.

I threw Tim a pair of knickers which I had bought the previous day along with one of my bras and a fresh pair of tights.

'Can you put those on yourself' I asked.

The knickers were again white but this time they were lacier than the ones he had worn yesterday. He looked at them, gulped and said, 'OK, I think so.' I thought the knickers and the tights would flatten him enough to wear the dress for today, so I said, as casually as I could, 'When you put the tights on, just push your cock back between your legs, it will help give you a nice flat front, no unsightly bulge. You can push your balls up too.'

He looked at me as if I had gone mad, 'What?'

I repeated myself and he shook his head, 'I can't do that, it's impossible.'

'I can assure you it's not, it's called tucking and yeah, it takes a bit of getting used to, but it's essential if you want to pass.'

Pushing my luck, I said, 'I can help you if you want.'

'Nooo, let me see what I can do myself.'

He disappeared to the bathroom and was back about 30 minutes later, red faced, wearing the bra and with the tights over the knickers.

'Well?' I asked.

'I cannot believe what I have just done, it's so fucking uncomfortable. I was just about to give up and come back out and tell you it was all off, when somehow they popped up inside. It felt so weird, still does.'

He looked down and said, 'They do drop down again don't they?'

I couldn't help laughing and got him flustered again.

'Please don't laugh at me, Philippa, this is all so difficult.'

'I'm sorry, babe, I promise I won't laugh any more.' I moved closer, gave him a big hug and a kiss, 'You're doing really well. Are you sure you haven't done this before?'

'No and if you're not careful I won't be doing it again.'

Time to shut up, Phil, I thought.

I handed him the breast forms which he slipped into the bra and I smiled to myself this time, as he jiggled about to get them to fit properly. He was getting the hang of this very quickly. I held the dress as he stepped into it and zipped it up. It hung a bit awkwardly at first but when I pulled the little belt tight the skirt flared out and it looked good on him. Once the wig was on and adjusted I got him to look in the mirror and he straight away started to check out what it looked like from the side and even over his shoulder to see the view from the back.

'Happy?'

He glanced at me, smiled and a little colour flushed his cheeks. 'Yes, I think so.'

I told him to sit on the sofa and he just sat down and immediately scrunched up the skirt of the dress.

'OK, first lesson, when you sit down in a skirt, you need to smooth it out under you before you sit on it otherwise you will crease it before you even start. And sit down gracefully, keeping your knees together, unless you want to flash your underwear at every man in the room.'

He blushed and looked a bit upset. 'Tina, don't get mad, you are doing this for the first time, I told you it takes practice.'

I showed him once and then asked him to do it again. It was a lot better this time and after i got him to do it twice more it began to look more natural.

Shoes came next and I had found a pair of black ankle boots with a cuban heel I thought would do the trick. They had two inch heel though and when I pulled them out Tim immediately said no, he would never wear heels.

'Heels? these aren't heels,' I said, 'look, just try them on see how you feel, we can go back to the others if you really want. I slid them onto his feet and luckily they did fit.

I held his hand and he tried to stand and immediately wobbled. I held on to him and he took a couple of steps and although he was a little unsteady, he managed better. I told him to take shorter steps and that made things a lot easier. He kept going and managed to walk up and down the room a couple of times.

'My God, it feels so different, but it's not as bad as I thought it would be.'

Wickedly I thought to myself, let him say that when I get him into a pair of five inch stilettos.

'Tina, we're only going to be able to scratch the surface over the next two days, but there are some things that we can work on to get you ready for your coming out on Saturday.

He pulled a face, 'I wish you wouldn't keep saying coming out like that.'

I tried to look innocent, failed badly and smirked instead.

'Okay, okay, I promise.'

I tried to remember when I started this journey and realised that I didn't have to unlearn anywhere near as much as Tim would have to. A lifetime of being male cannot be undone in a few hours, but there were some things that we could practice that would have change his mannerisms. I got him to walk slower with smaller steps than he usually would and to keep his elbows tucked in. This helped to reduce the more aggressive masculine stride he would usually adopt. I tried to get him to walk with one foot in front of the other and to sway his hips. After a few false starts, he began to move a little more easily than before. Tim said that he had done some ballroom dancing at school and so we tried a few limbering up exercises which also seemed to help.

By lunchtime, Tim's calves were beginning to ache and we took a break for some food. I suggested we go out to the local cafe, but he turned pale and refused outright. I made some sandwiches for us and while we were eating, I persuaded him to let me put nail varnish on his fingernails, only after swearing on my grandmother's grave that I would take it off later. I spent a lovely hour giving his nails and lovely burgundy colour and even with his short nails, it looked good. After they were done, Tim couldn't stop looking at them, but he outright refused to have his toenails done.

The rest of the afternoon was spent in more practice and it was obvious that Tim was getting more comfortable with what he was wearing and trying to follow what I was asking him to do. He was beginning, I thought, to move less stiffly and more gracefully than before. I got him to slow down his movements and to use his hands more when talking. I suspected Tim had just about reached the end of his tether by the late afternoon, so I called an end to practice and I brought through some white wine from the fridge and we both gratefully sank back onto the sofa. Tim now looked so much more comfortable in his dress and I thought he was learning fast. I just had to try to build on that confidence before Saturday night.

Tim asked me when it all started for me, so I told him my story from the beginning up to the present.

'Philippa, I'm not sure what to say. You've had to put up with so much to get here. That would have taken so much courage and guts to do what you've done.'

He reached over and hugged me tight.

'I don't know about courage,' I said, 'for me it was about wanting something so bad that you can't face living without it. It hurt me to think that I couldn't be who I wanted to be, who I needed to be really. It wasn't my choice, it was who I was already, I just had to get everybody else to see it. Some still don't, but that's their problem.'

He hugged me even tighter, and said, 'Someone once said it takes courage to grow up and become who you truly are. That's what you did.'

We drank a little more wine and I began to think about where to go tomorrow evening. There are a few more TG friendly pubs and clubs in London than there were, but it's not always easy to find a place for people from the community to get together without the intimidation you find in a straight place. There was a pub not too far from my apartment, The Cardinal Richelieu, which has a big party room where the landlord has a party every Saturday night which attracted a mixed crowd of crossdressers, Transgender girls, significant others and admirers. I knew Tim would be nervous, but I remembered it as a friendly place, where a first timer would be welcome. I called Emily from the kitchen, when Tim was using the toilet, to tell her what had happened between Tim and myself and what I had planned for Saturday at the Cardinal Richelieu.

'Are you sure you know what you're doing?' she asked.

'Think so, what do you mean?'

'You're taking this very seriously.'

'Catching these bastards is a serious matter, I want to put these arseholes away for a good long time.'

She paused, 'No, I mean you're taking this thing with Tim, or Tina, whoever, you're taking that very seriously.'

'It's one and the same thing, isn't it?'

'I hope so, Phil, I hope so. Just be careful, will you?'

'Yes, Mum, I will do, and I won't be late home, I promise.'

Emily laughed, called me a very rude word and rang off.

Tim still wouldn't go out anywhere dressed as he was, so I made a quick pasta for dinner and afterwards as we were sitting on the sofa with a drink, I confessed about the case involving Gareth Evans and the break in at the office together with the theft of the laptop and camera.

'Bloody hell, Philippa, why didn't you tell me before?'

'i didn't think it was relevant and I'm still not sure it is anyway.'

'I'll run some checks when I'm back at the station, but is there anything else you want to tell me, young lady?'

I bit my lip and peeked at him from behind my hair.

'No, Ma'am, nothing else. Have I been naughty? Will I have to be punished?'

'Oh yes, young lady, I think you will have to learn your lesson over my knee.'

'Don't you dare,' I squealed, but he was quick and had pulled me over his lap before I could stop him as he pushed my skirt up and started to slap my bum. He gave me a couple of whacks over my knickers but then I felt him pull them down and started slapping my bare bum.

'Oww, stop it you bastard, Tim, I'll get you for this, mark my words.'

He didn't stop and although he wasn't slapping me hard I could feel the sting as his hand hit my bare cheeks. I don't know exactly when it was the stings turned to warmth and I couldn't believe it but I began to feel turned on the whole scene. I could feel my cock getting harder as Tim continued to slap and I then I felt his cock start to grow and poke into me. I was moaning by this time and his slaps were getting weaker. I jumped up off his lap and pushed him back onto the sofa. I pulled my knickers down, threw them away and climbed onto the sofa so that I was pinning him down on his back.

He was laughing and I could feel his cock pushing up through his dress and against my bum. I grabbed his cock and squeezed.

'Oww, not fair.' he squeaked and I said, 'I told you I would get you back, buster.'

I gave his cock one last twist and he yelped again. I edged forwards up the sofa until my cock was bouncing around in front of his face. He stopped laughing and gave me a worried look.

'Hah, not laughing now are we? Tables are turned I see.'

I took hold of my cock and rubbed the head over his lips and around his mouth. He tried to keep his lips together but I held his nose and he had to open his mouth to breathe and I slipped my cock straight inside. he gagged a couple of times, but I stroked his head and said softly, 'Come on, just lick it, I did yours yesterday, it doesn't hurt. use your tongue.'

I almost jumped when I felt his tongue begin to lick the head of my cock. I looked down and he was almost asking me was this right? I nodded, 'That's great, Tim. Just keep doing what you're doing. Wrap your tongue around it, go on, you're doing fine. Now, move your head back and then forward so the head comes out and then back in. That's great, Tim. Now a little bit deeper and then back out again.'

His eyes were fixed on me all the time I was talking to him. 'You're doing fine, i'm really enjoying this, keep going. Now, let it slide out of your mouth and use your tongue to lick it up and down, oh, that's brilliant, that feels great. Doesn't this make feel like a girl? Sucking a cock, that's really girly, isn't it?'

His arms were trapped underneath me by my legs so I reached down and pulled my cock back against my tummy.

'Now lick your tongue up my cock, tim, that's right, from the bottom to the top, that feels so good. Ohhh, that feels so good, one more time, Tim. That's good, now wrap your lips around the tip and lick it with your tongue. That's so good, I love that, it feels so nice. Now take it right into your mouth and hold it there. That's right, keep using your tongue, but keep your teeth out of the way. That feels wonderful,Tim. Keep sucking and licking.'

I could feel I was getting close to cumming and I used my hand to stroke my cock as tim sucked the head.

'That's lovely, Tim. I can feel I'm going to cum soon, get ready, Tim.' His eyes widened and he shook his head. I smiled and pulled my cock out of his mouth just before I spurted cum all over his dress.

He spluttered and gagged a bit.

'Told you I would get you back, babe. Don't get mad, I wasn't going to cum in your mouth. Not this time anyway.'

'Shit, Philippa, I thought you were going to do it.'

I laughed, 'Never on a first date.'

I pulled him up from the sofa. 'Come on. let's get cleaned up and then I think it's bedtime.'

I pulled him over to the bathroom and told him to slip off the dress so I could put it in the wash. I got him to clean off his makeup and then we both undressed and shared the shower, soaping and washing and kissing each other until the water began to run cold. We dried each other and I led Tim into the bedroom.

'OK, remember it's all girl these two days, so you get to wear this beautiful nightdress. I handed him one of my favourite short nighties; pale blue silk, with lace at the hem and around the bodice, and a slit at one side. Tim looked at it suspiciously and I said, 'Go on, put it on. It won't bite you.'